Dimethylamine → (S)-2-tert-Butoxycarbonylamino-4-dimethylaminobutyric acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-4-bromo-2-tert-butoxycarbonylaminobutyric acid methyl ester (27.5 g, 93 mmol) in THF (100 mL) in a pressure reaction vessel was added triethylamine (26 mL) and dimethylamine (93 mL of 2.0 M in THF). The reaction vessel was sealed and heated to 60° C. for 16 hours and then cooled to room temperature. The reaction mixture was concentrated under reduced pressure and then dissolved in dichloromethane (500 mL). The solution was washed with water (3×200 mL) and brine (200 mL), dried over MgSO4, filtered through Celite and concentrated under reduced pressure. The residue was dried under high vacuum to afford 23.4 g of yellow oil (97% yield).

Provenance & Evidence